Low Point: In 1998 he overdosed after injecting himself with heroin and was sent to rehab. He's relapsed a few times since, although he was reportedly on the straight and narrow up until recently.
Enabler: CBS, which just offered him $1 million an episode to return to Two and a Half Men.
Rock Bottom: Since he was already in rehab when this current round of trouble with coke and hookers started, it may take another overdose, arrest, or running out of money to force him to get it together.
Odds of Recovery: Fair.
Low Point: Completely unemployable and now known more for her hard-partying and hard-shopping ways than her body of work, LiLo is having a tough time of it. But that's nothing compared to her two DUIs and three stints in rehab over the course of six months in 2007.
Enabler: The tabloid press.
Rock Bottom: Since she's currently functioning without work, supposedly not much money, and having failed at rehab as many times as she's failed at the box office, it's hard to imagine how much deeper she could sink without killing herself.
Odds of Recovery: Slim.
Low Point: The tales of Courtney's drug use and spendthrift ways have been around as long as she's been in the public eye. In 2003 she was arrested while breaking into her boyfriend and manager's house and later gave herself an accidental overdose of painkiller Oxycodone. She then lost custody of her daughter, and hasn't regained it.
Enabler: The Kurt Cobain estate.
Rock Bottom: She has been there for more than a decade.
Odds of Recovery: Slight.
Low Point: Unlike most of the others on this list, Cage's problem isn't drugs or booze—at least as far as we know—but his out-of-control spending. Thanks to all the debt he racked up, Cage lost two houses to foreclosure last year. Another was seized by the bank last week.
Enabler: The movie studios who keep hiring him.
Rock Bottom: He's there now.
Odds of Recovery: Good, if his movies can make some money.
Low Point: The singer who famously said no no no to rehab is also famous for her temper and tumultuous relationship with her ex-husband. It's all been pretty bad, but if we had to pick an incident, a 2008 arrest for drug possession and a videotape of her allegedly smoking crack probably takes the cake.
Enabler: Does she have any left?
Rock Bottom: She's going to have to have a serious overdose or some other traumatic event for her to see the light.
Odds of Recovery: Slim to none.
Low Point: Before she was just a tarted-up annoyance. But in the past few years she's become an total mess. The worst came before and after the death of "wife" Casey Johnson when Tila was publicly sharing strange naked videos of herself and freaking out on Twitter.
Enabler: Websites like RadarOnline.com which pay her for fake sonograms and "exclusive" videos.
Rock Bottom: When people stop paying attention to her.
Odds of Recovery: Fair. She used to be straight edge, so recovery is a possibility.
Low Point: This British answer to Paris Hilton is feeling the pressure after an alleged heroin-fueled naked romp that had something to do with Scientology. We don't know anything about that.
Enabler: Her father, Sir Bob Geldof's, sizable fortune.
Rock Bottom: She's got a long way to go. It will probably involve getting cut off from the family.
Odds of Recovery: She'll settle down in her 30s.
Low Point: Whitney looked like she was getting it together to release a "comeback" album, but recent reports have her concerts sucking and suggest she may be back on drugs. The worst was a 2002 Diane Sawyer interview where she laughably denied the drug allegations with instant classic catchphrases like "crack is whack."
Enabler: Concert promoters.
Rock Bottom: If admitting to having then-husband Bobby Brown pull a turd out of her ass on national TV wasn't bad enough, as soon as Oprah says she's disappointed in Whitney, she's at the bottom.
Odds of Recovery: Good, if her voice remains intact. If she loses her singing voice, she may be doomed.
Low Point: The British rocker became notorious last decade for his heroin use and relationship with model Kate Moss. He spent 14 weeks in prison in 2008 for a string of drug and driving offenses. But he's had nearly 30 brushes with the law over the last few years, including being arrested for possessing a controlled substance while leaving the courtroom and having heroin fall out of his coat while in court. Both of these were last year. He was arrested for drug-related reasons once again last month.
Enabler: Does he have a manager? Who keeps it together for this guy?
Rock Bottom: A fatal overdose.
Odds of Recovery: None.
Low Point: Known more as an "It" girl and partier than for her work on The O.C. and other shows, she was briefly committed to a psychiatric facility last summer.
Enabler: Any show crazy enough to hire her.
Rock Bottom: When she's no longer invited to fashion shows.
Odds of Recovery: Good—eventually.